CN110331605B - Natural dye color fixing agent and preparation method thereof - Google Patents
Natural dye color fixing agent and preparation method thereof Download PDFInfo
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- CN110331605B CN110331605B CN201910653025.4A CN201910653025A CN110331605B CN 110331605 B CN110331605 B CN 110331605B CN 201910653025 A CN201910653025 A CN 201910653025A CN 110331605 B CN110331605 B CN 110331605B
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F226/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
- C08F226/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a single or double bond to nitrogen
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/18—Introducing halogen atoms or halogen-containing groups
- C08F8/24—Haloalkylation
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/34—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using natural dyestuffs
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
- D06P5/02—After-treatment
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- D06P5/08—After-treatment with organic compounds macromolecular
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Abstract
The invention discloses a textile printing and dyeing color fixing agent, in particular to a natural dye color fixing agent which is a macromolecular compound containing a large amount of 3-chloro-2-hydroxypropyl, has high reactivity with hydroxyl and amino under alkaline conditions, can react with hydroxyl or amino in cotton, hemp and wool fibers in natural dye to form covalent bonds, and combines the natural dye which cannot react with the fabric fibers together through the covalent bonds; meanwhile, the invention also discloses a preparation method of the natural dye color fixing agent, which comprises the following steps of 1) carrying out polymerization reaction on dimethyl diallyl ammonium chloride and allyl amine monomers in water in the presence of ammonium persulfate; 2) adding epoxy chloropropane into water, dropwise adding ethylenediamine, controlling the reaction temperature to be not higher than 80 ℃, and after dropwise adding, keeping the temperature for a certain time at a certain temperature; 3) mixing the products of the step 1) and the step 2), and then preserving heat for a certain time at a certain temperature.
Description
Technical Field
The invention relates to a textile printing and dyeing color fixing agent, in particular to a natural dye color fixing agent and a preparation method of the natural dye color fixing agent.
Background
The natural dye is mainly derived from plants, animals or natural color ores, can be naturally degraded generally, most of the natural dye has no toxicity and side effects, and does not pollute the environment, and the characteristics make the natural dye increasingly become the key point of novel dye development. In addition, the dyeing of the natural dye is one of the ways of realizing clean dyeing and finishing and obtaining the ecological textile, the textile processed by the natural dye can meet the requirements of people on returning to the nature, and the ecological textile processing technology can be designed to improve the added value of textile products, so the method has rich development potential and wide application prospect.
However, the natural dye has a large particle size and a low affinity for textile fibers, resulting in poor color fastness and becoming a tragus stone for the popularization of natural dyes. Although in natural dye dyeing, mordanting and certain after-treatments can improve the fastness of dyeing, conventional mordants mostly contain heavy metal ions, many of which are listed in the banned list for ecological textiles. Mordants used in dyeing sometimes also affect the fading of the dye. For example, the color fading of onion becomes more severe with mordant alum and tin than with mordant chromium, iron and copper.
Disclosure of Invention
The invention aims to solve the defects of the prior art and provide a natural dye fixing agent capable of improving the dyeing fastness of natural dye, which is used for improving the soaping color fastness of natural dye dyed fabrics.
In order to achieve the purpose, the natural dye fixing agent designed by the invention is a high molecular polymer, and the structural units of the high molecular polymer are shown as a formula I, a formula II and a formula III:
wherein, in the formula I, the formula II and the formula III, a is a natural number between 550 and 1200, b is a natural number between 0 and 500, c is a natural number between 0 and 500, and b + c is 160-500, a + b + c is 800-1500;
compared with the traditional mordant dyeing method, the color fixing agent does not contain heavy metal, is harmless to the environment and human bodies, and is safer and more environment-friendly.
Meanwhile, the invention also provides a preparation method of the natural dye fixing agent, which comprises the following steps:
1) under the condition of existence of ammonium persulfate, carrying out polymerization reaction on dimethyl diallyl ammonium chloride and allyl amine monomers in water; wherein, the allylamine monomer is diallylamine, or monoallylamine, or the mixture of the two; the structure of the high molecular polymer synthesized in the step is shown as a formula IV;
in the formula IV, a is a natural number between 550 and 1200, b is a natural number between 0 and 500, c is a natural number between 0 and 500, a + b + c is 800-;
2) adding epoxy chloropropane into water, dropwise adding ethylenediamine, controlling the reaction temperature to be not higher than 80 ℃, and after dropwise adding, keeping the temperature at 50-80 ℃ for 1-4 hours; the structure of the compound synthesized in the step is shown as a formula V;
3) mixing the products of the step 1) and the step 2) according to the equal proportion of the amount of allylamine monomer substances contained in the products of the step 1) and the amount of ethylene diamine substances contained in the products of the step 2), and then preserving heat for 1-4 hours at 50-80 ℃; the structure of the compound synthesized in the step is shown as a formula VI;
in the formula VI, R is a structural unit shown as a formula VII;
in the formula VI, a is a natural number between 550 and 1200, b is a natural number between 0 and 500, c is a natural number between 0 and 500, a + b + c is 800-;
in the preparation method, in step 1), after the system of the dimethyldiallylammonium chloride, the allylamine monomer and the water is heated to 60 to 90 ℃ (specifically 60 to 85 ℃, 60 ℃, 65 ℃, 75 ℃ or 85 ℃), the aqueous solution of the ammonium persulfate is dripped into the system;
the dripping time can be 3-5 hours, specifically 3 hours, 4 hours or 5 hours;
the mass percentage content of the aqueous solution of ammonium persulfate can be 5-50%, specifically 10-50%, 10%, 20%, 30% or 50%;
the dosage of the ammonium persulfate can be 0.1-0.4% of the total mass of the dimethyldiallylammonium chloride and the allylamine monomer, and specifically can be 0.1%, 0.2%, 0.3% or 0.4%.
In the preparation method, in step 1), the temperature of the polymerization reaction may be 60 to 90 ℃, specifically 60 to 80 ℃, 60 ℃, 70 ℃, 80 ℃ or 90 ℃, and the time of the polymerization reaction may be 6 to 10 hours, specifically 6 hours, 7 hours, 8 hours, 9 hours or 10 hours;
in the step 1), the dosage of the dimethyl diallyl ammonium chloride is 77-92% of the total mass of the monomers, and specifically 77%, 82%, 87% or 92%;
in the step 1), the dosage of the allylamine monomer is 8-23% of the total mass of the monomer, specifically 8%, 13%, 18% or 23%;
in the step 1), the amount of water is 1-4 times of the total mass of the monomers, specifically 1 time, 2 times, 3 times or 4 times;
in the step 1), the total mass of the monomers is the total mass of the dimethyldiallylammonium chloride and the allylamine monomers;
in the step 2), the dosage of the ethylenediamine is A mol, the dosage of the epichlorohydrin is A multiplied by 4mol, and the dosage of the water is 1-4 times of the total mass of the ethylenediamine and the epichlorohydrin, specifically 1 time, 2 times, 3 times or 4 times;
in the step 2), the heat preservation temperature is 50-80 ℃, and specifically can be 50 ℃, 65 ℃, 70 ℃ or 80 ℃;
in the step 2), the heat preservation time is 1-4 hours, specifically 1 hour, 2 hours, 3 hours or 4 hours;
in the step 3), the amount of allylamine monomer substances contained in the product in the step 1) is equal to the amount of ethylenediamine substances contained in the product in the step 2);
in the step 3), the heat preservation temperature is 50-80 ℃, and specifically can be 50 ℃, 60 ℃, 70 ℃ or 80 ℃;
in the step 3), the heat preservation time is 1-4 hours, specifically 1 hour, 2 hours, 3 hours or 4 hours;
in the molecular structure of the synthesized natural dye color fixing agent, quaternary ammonium salt cations in the structural unit shown in the formula I can be combined with anions in the molecular structure of the natural dye, so that the fastness of the natural dye is improved; the five-membered ring structures in the structural units of the formula I and the formula II are beneficial to increasing the affinity of the natural dye fixing agent molecules to the fabric, so that the natural dye fixing agent is easier to adsorb on the fabric, and the color fastness is improved; the 3-chloro-2-hydroxypropyl in the structural units of the formulas II and III can react with the natural dye to neutralize hydroxyl or amino in cotton, hemp and wool fibers under alkaline conditions to form covalent bonds, so that the natural dye and the textile fibers are combined in a covalent bond mode, and the color fastness is improved.
Compared with the prior art, the invention has the following advantages:
(1) the natural dye color fixing agent contains a cationic structure, and can be combined with anions in a natural dye molecular structure, so that the natural dye and the natural dye color fixing agent form water-insoluble color lake, and the color fastness is improved;
(2) the natural dye color fixing agent contains a ring structure, has strong affinity to both fabrics and natural dyes, is favorable for actively adsorbing the natural dye onto the fabrics during dipping and use, and simultaneously prevents the natural dye from falling off from the fabrics during washing;
(3) the natural dye color fixing agent contains a large amount of 3-chloro-2-hydroxypropyl, has high reactivity with hydroxyl and amino under alkaline conditions, can react with hydroxyl or amino in natural dye neutralization cotton, hemp and wool fibers to form covalent bonds, thereby playing a role of 'bridges', and combines the natural dye which cannot react originally and the fabric fibers together through the covalent bonds, thereby improving the color fastness.
Drawings
FIG. 1 is an infrared spectrum of a natural dye fixing agent prepared in example 1 of the present invention;
FIG. 2 is an infrared spectrum of a natural dye fixing agent prepared in example 2 of the present invention;
FIG. 3 is an IR spectrum of a natural dye fixing agent prepared in example 3 of the present invention;
fig. 4 is an infrared spectrum of the natural dye fixing agent prepared in example 4 of the present invention.
Detailed Description
The experimental procedures used in the following examples are all conventional procedures unless otherwise specified.
Materials, reagents and the like used in the following examples are commercially available unless otherwise specified. Wherein the content of the dimethyl diallyl ammonium chloride is 60%, and the content of the diallyl amine, the monoallyl amine, the ammonium persulfate, the ethylenediamine and the epichlorohydrin is more than 99%.
The application process of the natural dye fixing agent in the following embodiment of the invention is as follows: dyeing the fabric with natural dye, padding the fabric with working solution, and drying. The working solution contains 10-40g/L of natural dye color fixing agent and 10g/L of sodium carbonate.
The soaping fastness of the fabric is tested according to the method C (3) in GB/T3921-2008 soaping color fastness test for textiles.
Example 1
Firstly, preparing natural dye color fixing agent
Step 1), adding 106 kg of dimethyldiallylammonium chloride, 5.7 kg of monoallylamine and 63 kg of deionized water into a reactor, heating to 90 ℃, dropwise adding an ammonium persulfate aqueous solution (0.07 kg of ammonium persulfate is dissolved in 1.33 kg of deionized water), finishing dropwise adding within 3 hours, and then preserving heat at 90 ℃ for 6 hours, thus finishing the process.
And 2), adding 37 kg of epoxy chloropropane and 64.5 kg of deionized water into the reactor, dropwise adding 6 kg of ethylenediamine, controlling the temperature to be not higher than 70 ℃ in the process, continuously preserving the heat at 70 ℃ for 3 hours after the dropwise adding is finished, and finishing the process.
And 3) mixing the products obtained in the step 1) and the step 2), uniformly stirring, heating to 50 ℃, and preserving heat for 4 hours to finish.
The molecular structure of the synthesized natural dye fixing agent is shown as a formula VIII:
fig. 1 is an infrared spectrum of the natural dye fixing agent prepared in example 1 of the present invention. 3370cm in the figure-11121cm is the hydroxyl group O-H stretching vibration absorption peak-1The molecular structure is proved to contain hydroxyl groups and indirectly proved to contain 3-chloro-2-hydroxypropyl groups. 2945cm-1Is represented by-CH2Absorption peak of stretching vibration of-1477 cm-1Is classified into and+linked dimethyl (CH)3)2Typical symmetric bending vibration of 1250cm-1Is the stretching vibration peak of C-N bond in the carbon-nitrogen five-membered heterocycle.
Second, natural dye color fixing agent application effect
And (3) padding a working solution containing 20g/L of the natural dye fixing agent synthesized in the embodiment 1 and 10g/L of sodium carbonate into the mulberry, purple and pomegranate natural dye dyed fabric, and drying. The fixing effect is shown in table 1.
Table 1: fixation effect of the Natural dye fixing Agents in example 1
Example 2
Firstly, preparing natural dye color fixing agent
Step 1), adding 53.3 kg of dimethyldiallylammonium chloride, 9.7 kg of diallylamine and 20.4 kg of deionized water into a reactor, heating to 60 ℃, dropwise adding an ammonium persulfate aqueous solution (0.09 kg of ammonium persulfate is dissolved in 0.81 kg of deionized water) for 4 hours, and then keeping the temperature at 60 ℃ for 8 hours to finish the process.
And 2), adding 37 kg of epoxy chloropropane and 43 kg of deionized water into the reactor, dropwise adding 6 kg of ethylenediamine, controlling the temperature to be not higher than 60 ℃ in the process, and continuously preserving the heat at 60 ℃ for 2 hours after the dropwise adding is finished, thus finishing the process.
And 3), mixing the products obtained in the step 1) and the step 2), uniformly stirring, heating to 60 ℃, and preserving heat for 3 hours to finish.
The molecular structure of the synthesized natural dye fixing agent is shown as formula IX:
fig. 2 is an infrared spectrum of the natural dye fixing agent prepared in example 2 of the present invention. 3370cm in the figure-11123cm as the O-H stretching vibration absorption peak of hydroxyl-1The molecular structure is proved to contain hydroxyl groups and indirectly proved to contain 3-chloro-2-hydroxypropyl groups. 2947cm-1Is represented by-CH2Absorption peak of stretching vibration of-1472 cm-1Is classified into and+linked dimethyl (CH)3)2Typical symmetric bending vibration of 1248cm-1Is the stretching vibration peak of C-N bond in the carbon-nitrogen five-membered heterocycle.
Second, natural dye color fixing agent application effect
And (3) padding a natural dye dyed fabric of mulberries, purple clay and pomegranate with a working solution containing 10g/L of the natural dye color fixing agent synthesized in the embodiment 2 and 10g/L of sodium carbonate, and drying. The fixing effect is shown in table 2.
Table 2: fixation effect of Natural dye fixing Agents in example 2
Example 3
Firstly, preparing natural dye color fixing agent
Step 1), adding 80 kg of dimethyldiallylammonium chloride, 9.7 kg of diallylamine and 156 kg of deionized water into a reactor, heating to 70 ℃, dropwise adding an ammonium persulfate aqueous solution (0.23 kg of ammonium persulfate is dissolved in 0.23 kg of deionized water), finishing dropwise adding within 5 hours, and then preserving heat at 70 ℃ for 7 hours, thus finishing the process.
And 2), adding 37 kg of epoxy chloropropane and 100 kg of deionized water into the reactor, dropwise adding 6 kg of ethylenediamine, controlling the temperature to be not higher than 80 ℃ in the process, and continuously preserving the heat at 80 ℃ for 1 hour after the dropwise adding is finished, thus finishing the process.
And 3) mixing the products obtained in the step 1) and the step 2), uniformly stirring, heating to 70 ℃, and preserving heat for 2 hours to finish.
The molecular structure of the synthesized natural dye fixing agent is shown as the formula X:
fig. 3 is an infrared spectrum of the natural dye fixing agent prepared in example 3 of the present invention. 3380cm in the figure-11120cm which is the hydroxyl group O-H stretching vibration absorption peak-1The molecular structure is proved to contain hydroxyl groups and indirectly proved to contain 3-chloro-2-hydroxypropyl groups. 2940cm-1Is represented by-CH2-absorption peak of stretching vibration of 1478cm-1Is classified into and+linked dimethyl (CH)3)2Typical symmetrical bending vibration of 1259cm-1Is the stretching vibration peak of C-N bond in the carbon-nitrogen five-membered heterocycle.
Second, natural dye color fixing agent application effect
And (3) padding a mulberry, purple and pomegranate natural dye dyed fabric into a working solution containing 30g/L of the natural dye color fixing agent synthesized in the embodiment 3 and 10g/L of sodium carbonate, and drying. The fixing effect is shown in table 3.
Table 3: fixation effect of Natural dye fixing Agents in example 3
Example 4
Firstly, preparing natural dye color fixing agent
Step 1), adding 66.7 kg of dimethyldiallylammonium chloride, 4.85 kg of diallylamine, 2.85 kg of monoallylamine and 164 kg of deionized water into a reactor, heating to 80 ℃, dropwise adding an ammonium persulfate aqueous solution (0.14 kg of ammonium persulfate is dissolved in 0.33 kg of deionized water), finishing dropwise adding for 5 hours, and then preserving heat at 80 ℃ for 6 hours to finish the process.
And 2), adding 37 kg of epoxy chloropropane and 172 kg of deionized water into the reactor, dropwise adding 6 kg of ethylenediamine, controlling the temperature to be not higher than 90 ℃ in the process, and continuously preserving the heat for 4 hours at 90 ℃ after the dropwise adding is finished, thus finishing the process.
And 3) mixing the products obtained in the step 1) and the step 2), uniformly stirring, heating to 80 ℃, and preserving heat for 1 hour to finish.
The molecular structure of the synthetic natural dye fixing agent is shown as formula XI:
fig. 4 is an infrared spectrum of the natural dye fixing agent prepared in example 4 of the present invention. 3380cm in the figure-11122cm as the OH group O-H stretching vibration absorption peak-1The molecular structure is proved to contain hydroxyl groups and indirectly proved to contain 3-chloro-2-hydroxypropyl groups. 2930cm-1Is represented by-CH2Absorption peak of stretching vibration of-1472 cm-1Is classified into and+linked dimethyl (CH)3)2Typical symmetric bending vibration of 1248cm-1Is the stretching vibration peak of C-N bond in the carbon-nitrogen five-membered heterocycle.
Second, natural dye color fixing agent application effect
And (3) padding a mulberry, purple and pomegranate natural dye dyed fabric into a working solution containing 40g/L of the natural dye color fixing agent synthesized in the embodiment 4 and 10g/L of sodium carbonate, and drying. The fixing effect is shown in table 4.
Table 4: fixation effect of Natural dye fixing Agents in example 4
Claims (1)
1. A preparation method of a natural dye fixing agent is characterized in that the natural dye fixing agent is a macromolecular compound, and the molecular structure of the natural dye fixing agent contains the following structural units:
wherein, in the formula I, the formula II and the formula III, a is a natural number between 550 and 1200, b is a natural number between 0 and 500, c is a natural number between 0 and 500, a + b + c is 800-;
which comprises the following steps:
1) under the condition of existence of ammonium persulfate, carrying out polymerization reaction on dimethyl diallyl ammonium chloride and allyl amine monomers in water; the allylamine monomer is diallylamine, or monoallylamine, or a mixture of the two;
2) adding epoxy chloropropane into water, dropwise adding ethylenediamine, controlling the reaction temperature to be not higher than 80 ℃, and after dropwise adding, keeping the temperature for a certain time at a certain temperature;
3) mixing the products of the step 1) and the step 2), and keeping the temperature for a certain time at a certain temperature;
in the step 1), heating a system of the dimethyldiallylammonium chloride, the allylamine monomer and the water to 60-90 ℃, and then dropwise adding the aqueous solution of the ammonium persulfate into the system;
the dripping time is 3-5 hours;
the mass percentage of the aqueous solution of ammonium persulfate is 5-50%;
the dosage of the ammonium persulfate is 0.1 to 0.4 percent of the total mass of the dimethyl diallyl ammonium chloride and the allyl amine monomer;
in the step 1), the temperature of the polymerization reaction is 60-90 ℃, and the time of the polymerization reaction is 6-10 hours;
in the step 1), the dosage of the dimethyl diallyl ammonium chloride is 77-92% of the total mass of the monomers, and the dosage of the allyl amine monomer is 8-23% of the total mass of the monomers;
the using amount of the water is 1-4 times of the total mass of the monomers;
the total mass of the monomers is the total mass of the dimethyldiallylammonium chloride and the allylamine monomers;
in the step 2), the using amount of the ethylenediamine is A mol, the using amount of the epichlorohydrin is A multiplied by 4mol, and the using amount of the water is 1-4 times of the total mass of the ethylenediamine and the epichlorohydrin;
in the step 2), the heat preservation temperature is 50-80 ℃, and the heat preservation time is 1-4 hours;
in the step 3), the amount of allylamine monomer substances contained in the product in the step 1) is equal to the amount of ethylenediamine substances contained in the product in the step 2);
in the step 3), the heat preservation temperature is 50-80 ℃, and the heat preservation time is 1-4 hours.
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| CN111041862A (en) * | 2019-10-25 | 2020-04-21 | 深圳市迪威科技有限公司 | Method for modifying and dyeing all-cotton fabric |
| CN115726203A (en) * | 2021-08-31 | 2023-03-03 | 传清化工(广东)有限公司 | Polyester cotton high-fastness fixing agent and preparation method thereof |
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